Chlorinated methyl-ether of menthol.



45 acid gas.

UNITED STATES PATENT OFFICE.

EDGAR VVEDEKINI), OF

TUBTNGEN, GERMANY.

CHLORINATED METHYL-ETHER OF MENTHOL.

SPECIFICATION forming part of Letters Patent No. 703,104, dated June 24, 1902.

Application filed February 25, 1902. Serial No. 95,586. (Specimens) dom of lVui-temberg, German Empire, have invented a new Chlorinated Methyl-Ether of Menthol, of which the following is a specification.

This invention consists in a chlorinated 1o methyl ether of menthol which corresponds tothe formula O H OOH Cl, and which is consequently a chloromethyl-menthyl-ether. This compound is particularly suitable for treating catarrhal affections of the respira- I 5 tory passages, since it can be readily split up by simple means, so as to liberate or evolve therapeutically-active constituents-namely, formic aldehyde and menthol-which can be inhaled or introduced into the respiratory 2o passages by the nose or mouth of the patient.

The new product chloromethyl-menthylether is a yellow oily liquid of peculiar and somewhat pungent odor. The liquid is insoluble in water and alcohol, but dissolves 2 5 readily in ether and chloroform. It possesses a specific gravity of about 0.9821 and a boil ing-point of about 160 to 163 centigradeunder thirteen to sixteen millimeters pressure and rotates the plane of polarization to the go left.

In the manufacture of this new product I may proceed in accordance with the following example; but it will be understood that I do not limit myself to the exact proportions,

temperatures, and other details specified,

which may be varied without departing from the spirit of the invention.

Example: One hundred and sixty grams of menthol are mixed with ninety grams of a thirty-five-per-cent. formalin solution, and

the mixture is brought into solution by carefully heating on the water-bath. Into the well-stirred mixture is introduced during two to three hours an excess of dry hydrochloric- Two layers will form, the upper of which is decanted off and dried for twentyfour hours over a bed of calcined sulfate of soda. After filtration and pressing of the desiccated material the limpid oil is freed 5 from the greater part of the dissolved hydrochloric acid by injecting into in it in cacao a current of dry air. By repeating this operation at a temperature of to centigrade the remainder of the hydrochloric-acid gas is caused to escape. The average yield of the ether thus obtained amounts to a little more than the quantity of menthol employed.

The therapeutic efiect of the chloromethylmenthyl-ether is based upon the great facility with which it can be decomposed, so as to liberate or evolve the substances before described. This decomposition is, for instance, effected if the substance be exposed to the action of moist air and still more rapidly if it be introduced into hot water or alkalies. Upon being thus decomposed it splits up into formic aldehyde, menthol, and hydrochloric acid. In this way the therapeutically-active bodies are obtained in a nascent state.

In employing the improved compound for inhalationsfor example, in the treatment of catarrhal afiections of the respiratory passagesI may, according to myinvention, introduce the said compound into hot water or into a hot alkaline solution contained in a suitable vessel provided with leading or delivery tubes adapted to be inserted into the mouth or nostrils of the patient.

The rapidity of the decomposition depends upon the temperature of the decomposing agent. The higher this is the more rapidly does the decomposition take place. The hydrochloric acid liberated remains dissolved in the water, while formic aldehyde and menthol escape with the aqueous vapors. By inhaling these aqueous vapors saturated with formic aldehyde and menthol into the airpassages catarrhal affections of the latter can be quickly relieved or cured.

It will be understood that instead of employing hot water or an alkaline solution, as above described, to cause the decomposition of the compound I may effect this by any other suitable meansfor example, by exposing the compound in a suitable vessel to the action of moist air, means being provided to absorb the hydrochloric acid as same is evolved.

I claim--' As a new article of manufacture the improved product hereinbefore described being a chlorinated inethyl ether of menthol corresponding to the formula O H OCH CI and ence of two witnesses, this 8th day of Februbeing a yellow oily liquid of peculiar pungent ary, 1902. odor, of specific gravity about; 0.9821, insoluble in water and alcohol and readily soluble EDGAR WEDEKIND' 5 in ether and chloroform. Witnesses:

In testimony that I claim the foregoing as M. HAHN,

my invention I have signed my name, in pres- IRNST ENTENMAs. 

